Why does the Torah write "Vayavo ad Chevron" in the singular?
Rashbam #2 and Targum Yonasan: It refers to all the Spies, each of whom traveled to Chevron. 3
How could Cham build Chevron for Cana'an his youngest son before Tzo'an, his oldest son?
Rashi: What the Torah means is that Chevron - the worst part of Eretz Cana'an 1 was seven times nicer than Tzo'an 2 - the best part of Egypt, 3 which itself the Torah describes as "the garden of Hashem". 4
Who was Anak?
Ramban #1: Refer to 13:22:4:1.
Ramban #2: "Anak" means 'giants' - In fact, the father of Achiman, Sheishai and Talmai was Arba, so- called because together with his sons, they numbered four giants - and "Avi Anak" means 'the father of the giants'.
Why does the Torah see fit to inform us that Chevron was built before Tzo'an?
Rashi: Refer to 13:21:2:1**.
Ramban #1: Chevron is synonymous with Kiryas Arba, so-called because Arba 1 - the original giant built it for his son Anak, 2 the father of the Anakim 3 (Achiman, Sheishai and Talmai), which explains why the Torah writes here "ve'Sham Achiman, Sheishai and Talmai Yelidei ha'Anak". And the Torah is coming to teach us the power of the Anakim 4 - whose longevity matched their height.
Rashbam: Yisrael were aware of the importance of Tzo'an, so the Pasuk points out that Chevron was built before Tzo'an and was therefore more important than it. 5 Moreover, it is pointing out how the giants, who were from the earlier generations, still lived there.
Ramban: See Yehoshua, 14:15. Targum Yonasan also explains that 'Anak' is the name of a man, and not a word that means 'giants'.
Ramban: The father of the giants (See R. Chavel's footnotes.
Ramban: Who were called by that name in account of their tall and handsome appearance - like Anakim (necklaces) to the throat - See Mishlei, 1:9.
Ramban: Bearing in mind that Arba built Chevron before Tzo'an was built.
Rashbam: Since the older the town, the more esteemed it is.